Record Information
Version1.0
Creation date2010-04-08 22:08:19 UTC
Update date2015-10-09 22:28:40 UTC
Primary IDFDB008937
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Aminobutyric acid
Descriptiongamma-Aminobutyric acid is the chief inhibitory neurotransmitter in the mammalian central nervous system. It plays a role in regulating neuronal excitability throughout the nervous system. In humans, GABA is also directly responsible for the regulation of muscle tone. [Wikipedia]
CAS Number56-12-2
Structure
Thumb
Synonyms
SynonymSource
3-Carboxypropylaminebiospider
4-amino-butanoic acidbiospider
4-Amino-n-butyric acidbiospider
4-Aminobutanoatebiospider
4-Aminobutanoic acidbiospider
4-Aminobutylatebiospider
4-Aminobutyratebiospider
4AbuChEBI
AminalonHMDB
Aminobutanoic acidbiospider
Aminobutyric acidbiospider
Aminobutyric acid,-4-, αbiospider
Butanoic acid, 4-amino- (9CI)biospider
Butyric acid, 4-amino-biospider
DL-gamma-amino-n-butyric acidbiospider
g-amino-BUTANOateGenerator
g-amino-BUTANOic acidGenerator
g-amino-N-ButyrateGenerator
g-amino-N-Butyric acidGenerator
g-AminobutanoateGenerator
g-Aminobutanoic acidGenerator
g-AminobuttersaeureGenerator
g-AminobutyrateGenerator
g-aminobutyric acidbiospider
GABAbiospider
Gaballonbiospider
Gamarexbiospider
Gamastanbiospider
Gamma aminobutyratebiospider
Gamma aminobutyric acidbiospider
Gamma-amino butyric acidbiospider
gamma-amino-BUTANOateGenerator
Gamma-amino-butanoic acidbiospider
gamma-amino-N-ButyrateGenerator
Gamma-amino-n-butyric acidbiospider
gamma-AminobutanoateGenerator
Gamma-aminobutanoic acidbiospider
Gamma-aminobutryic acidbiospider
gamma-AminobuttersaeureChEBI
Gamma-aminobutyratebiospider
Gamma-aminobutyric acidbiospider
Gamma(amino)-butyric acidbiospider
Gammageebiospider
GammalonHMDB
Gammalon (TN)biospider
GammaloneHMDB
Gammarbiospider
Gammasolbiospider
Gamulinbiospider
Mielogenbiospider
Mielomadebiospider
Omega-aminobutyrateGenerator
Omega-aminobutyric acidChEBI
Piperidatebiospider
Piperidic acidbiospider
Piperidinatebiospider
Piperidinic acidbiospider
Reanalbiospider
W-AminobutyrateHMDB
W-Aminobutyric acidHMDB
γ-amino-butanoateGenerator
γ-amino-butanoic acidGenerator
γ-amino-N-butyrateGenerator
γ-amino-N-butyric acidGenerator
γ-aminobutanoateGenerator
γ-aminobutanoic acidGenerator
γ-aminobuttersaeureGenerator
γ-aminobutyrateGenerator
γ-aminobutyric acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility365 g/LALOGPS
logP-3ALOGPS
logP-2.9ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)4.53ChemAxon
pKa (Strongest Basic)10.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.46 m³·mol⁻¹ChemAxon
Polarizability10.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H9NO2
IUPAC name4-aminobutanoic acid
InChI IdentifierInChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
InChI KeyInChIKey=BTCSSZJGUNDROE-UHFFFAOYSA-N
Isomeric SMILESNCCCC(O)=O
Average Molecular Weight103
Monoisotopic Molecular Weight103
Classification
DescriptionThis compound belongs to the class of chemical entities known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Amino fatty acid
  • Straight chain fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point203 oC
Boiling PointNot Available
Experimental Water Solubility1300 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-3.17HANSCH,C ET AL. (1995)
Experimental pKa4.05
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dj-1900000000-f831f79dfcaeffa8b177View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-2de9d92a2cfc7bc655f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-73bbf2ee0803f058dbedView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1901000000-85d4bd98af8534428b5aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-0900000000-6be23968e972a414be51View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-9a224763afd8ca892addView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9800000000-d8906d09ca1872a6391cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1900000000-54db7e21790401045519View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-1901000000-b047af158215c2b5b8e8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-21ea76dfb0da62031f1dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0901000000-5d60b0a446fd8122f613View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-1900000000-f831f79dfcaeffa8b177View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-2de9d92a2cfc7bc655f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-73bbf2ee0803f058dbedView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1901000000-85d4bd98af8534428b5aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0900000000-6be23968e972a414be51View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-9a224763afd8ca892addView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9800000000-d8906d09ca1872a6391cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1900000000-54db7e21790401045519View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-1901000000-b047af158215c2b5b8e8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-1900000000-1219470a0be188da64e6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0900000000-f7117dfaf9d856c95919View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-1900000000-e35585a985d8128d044eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-d5f55a414ff1e8c65d9dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9700000000-4b2809309587240dd479View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uxr-8900000000-ce0d8f44422836cd9965View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0005-9000000000-8ce5afb97d7c08821da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0005-9100000000-32c433b2c916697690f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-5831aaabdf53f3132ae5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-9babfd4a6937ecba7318View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-9000000000-e1c0c1485d846e9b123bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-647d55ecf98850e7a875View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-7c107641a38922c88fcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-86718b349efad6334e3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-a1e84e55e4b6c6628d5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-0009000000-29c22bf0ed844d09c0afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-1d00adad47e42c60c340View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-1900000000-47b195fb74720cc99464View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9000000000-a14a52dc59bf9988bb44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-5900000000-20c55b2809389d5ad83bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9000000000-eca4c5aefca98751a11eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014j-9000000000-f0783316e09291749409View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0005-9000000000-81837eb9c0b926cb0e81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0005-9000000000-8b48126992d7fa242636View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-9000000000-7d4636efbc4e5d75872eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-655f9d93a35bfa537583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ku-9000000000-4a334d5e272576f62403View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4a13b03446b3370ccd43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-655f9d93a35bfa537583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ku-9000000000-4a334d5e272576f62403View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-dbf4f9e19a35f953a189View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID116
ChEMBL IDCHEMBL96
KEGG Compound IDC00334
Pubchem Compound ID119
Pubchem Substance IDNot Available
ChEBI ID16865
Phenol-Explorer IDNot Available
DrugBank IDDB02530
HMDB IDHMDB00112
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID165
Dr. Duke IDGABA|GAMMA-AMINOBUTYRIC-ACID
BIGG ID34652
KNApSAcK IDC00001337
HET IDABU
Flavornet IDNot Available
GoodScent IDrw1198861
SuperScent IDNot Available
Wikipedia IDGABA
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
analeptic35337 Any drug that enhances the activity of the central nervous system.DUKE
anti cephalagic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cerebrotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti choreic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti insomniac52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti insomnic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti lethargic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti stress52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti tinniticDUKE
anxiolytic35474 Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.DUKE
cardiovascular38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
central nervous system inhibitor35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hypotensiveDUKE
neuro inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
neurotransmitter25512 An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
tranquilizerDUKE
Enzymes
NameGene NameUniProt ID
Glycine amidinotransferase, mitochondrialGATMP50440
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Glutamate decarboxylase 2GAD2Q05329
Glutamate decarboxylase 1GAD1Q99259
Arginine decarboxylaseADCQ96A70
Glutamine synthetaseGLULP15104
Probable glutamate--tRNA ligase, mitochondrialEARS2Q5JPH6
Gamma-aminobutyric acid receptor-associated protein-like 2GABARAPL2P60520
Pathways
NameSMPDB LinkKEGG Link
Glutamate MetabolismSMP00072 map00250
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
savory
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
meaty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).